1- It is possible that you were still logged in to @mydomain.com while you 
were using @gmail.com when you were trying to access @mydomain GAE site. 

2- The incognito mode test that you made was a good idea. Clearing browser 
sessions and/or cookies works, too. And to make sure that your test 
environment is not tainted, I recommend testing the access of @gmail.com in 
a completely separate computer.

3. To use custom domains with HTTPS, you must first activate and configure 
SSL for App Engine with your domain. 
<https://cloud.google.com/appengine/docs/python/console/using-custom-domains-and-ssl#adding_ssl_to_your_custom_domain>
 I 
also found this similar thread on StackOverflow 
<https://stackoverflow.com/questions/16469219/secure-always-parameter-is-ignored-in-appengine>
.

If the above does not mitigate your issue, I highly encourage you to submit 
a defect report <https://issuetracker.google.com> as described in this 
article <https://developers.google.com/issue-tracker/> so that proper 
attention will be given to it. You can also refer on this thread, if 
required. 

 

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